Reaction of N, N-dimethyl-2-triorganosilylethylamines with benzyne

Y Sato, Y Ban, T Aoyama, H Shirai

Index: Sato,Y. et al. Journal of Organic Chemistry, 1976 , vol. 41, p. 1962 - 1965

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Citation Number: 16

Abstract

Reaction of N, N-dimethyl-2-triorganosilylethylamines (la-d) with benzyne, produced from o- fluorobromobenzene and n-butyllithium, gave N-methyl-N-triorganosilylmethylanilines (2a- d), 1-methyl 3, 3-disubstituted benzo [d]-1, 3-azasilolines (3b-d), N, N-dimethylaniline (51, and triorganovinylsilanes (6a-d). It was revealed that the cyclization giving 3 was induced in the presence of excess n-butyllithium. The reaction mechanism also is discussed.